When 49ers Enterprises took over from former Leeds United owner Andrea Radrizzani, it brought a dramatic period in West Yorkshire to an end – a period during which the Whites finally returned to the Premier League after well over a decade away.
That return to the Premier League – and the battle to stay in it – saw plenty of transfer business at Elland Road as they battled to stay afloat. Some of it was exceptional, but some of it really, really wasn’t.
Football FanCast has taken a look at the worst of Radrizzani’s tenure to see where things eventually went wrong.
6 Dishonourable mention: Weston McKennie
We just have to give a quick shoutout to McKennie. Leeds signed him on loan from Juventus in January 2023 in an attempt to save their season, but the American flopped wildly. It was so bad that fans were letting him know just how out of shape he was as they said goodbye at the end of the season.
There was a clause in the loan contract, however, that would have made it permanent for £34m, and the only reason that’s not happening? The relegation. A bizarre situation where fans would prefer McKennie was topping this list as an all-time bad transfer. Instead, he’ll depart. Bullet dodged. Sort of.
5 Hélder Costa – £15m
Leeds signed Hélder Costa from Wolves back in 2019, initially on loan. And his inclusion in this list is perhaps a bit harsh – Costa did play a role in their eventual promotion that season.
However, the deal became permanent in July 2020 for around £15m, per the Mirror. Once permanent, Costa struggled and never truly got to grips with the Premier League – only three goals in 25 appearances. He’s now spent the last two seasons off on loan, first with Valencia and then Al-Ittihad in Saudi Arabia.
4 Daniel James – £25m
James was a sizeable signing for Leeds, joining from Manchester United at the end of the 2021 summer transfer window for £25m. He’s a player they’d wanted for a while and things initially looked good.
But then Radrizzani made the wildly unpopular decision to sack Marcelo Bielsa the following February. James then never fit in under new boss Jesse Marsch and was sent out on loan just a year after arriving. He subsequently spent the season finishing 10th with Fulham while Leeds went down.
3 Brenden Aaronson – £25m
Aaronson is only 22 and could still go on to become a fantastic player. He may well go on to be a brilliant signing for Leeds. The problem, though, is that the American arrived at the start of last season as their big summer signing.
Paying £25m for a player who then struggled is bad. It’s even worse when your entire team struggles to the point of relegation. It’s just not a good look for the club when that player is 22 and moving from the Austrian Bundesliga.
If Leeds had made a less risky signing, it really could have been enough to keep them up.
2 Georginio Rutter – £36m
Leeds needed help in the January transfer window. You can argue all day where they needed that help but a new striker undoubtedly could have made a major difference. They went out and paid a club-record £36m for Rutter from Hoffenheim – an enormous risk, given he had two goals in 15 games by that point in the season.
It was a disaster. Rutter played 273 minutes in total – so barely the equivalent of three full games – and failed to score once. He did register an assist, but splashing out £36m for one assist isn’t exactly value for money.
The really worrying part about this one, though, is that Radrizzani didn’t want to make the signing. Per The Athletic, he favoured a loan move with an option to buy. It was the 49ers Group – which is about to take over 100% of Leeds – that pushed for the big permanent deal.
1 Jean-Kévin Augustin – £25m, sort of.
If the Rutter deal scares fans at all, they can rest easy that it’s almost impossible for any subsequent transfer to be worse than Radrizzani’s worst. The Augustin debacle is an all-timer.
Leeds signed the Frenchman on loan from RB Leipzig in January 2020. There was an option to buy him permanently for £17.7m, per Bild, but that option became an obligation if the West Yorkshire club were promoted at the end of the season.
Now, Leeds were promoted, of course, but then tried to argue that they hadn’t been. See, ‘end of the season’ is the key phrase here because they argued that June 30th was the end of the season as per the contract. In the year of the pandemic, however, the season was delayed and the club technically weren’t promoted by that ‘end of the season’. The promotion came in early July, so they sent him back to Leipzig without triggering the clause.
Leipzig took that to court, though, saying that Leeds quite clearly earned promotion that year and needed to pay for Augustin. They won that case – forcing Leeds to actually pay more in a breach of contract suit – a sum of £25m, per the Athletic.
Leeds, then, paid £25m for a player they didn’t actually buy. The kicker is that Augustin played a total of 48 minutes for the club, making every facet of this a disaster.